This is a little hint for you guys who hate getting caught by the guards and then having all your beloved swag swiped by those pesky legionnaires.

Once you've payed the fine or done your sentence, just go back into the prison barracks or dungeon, wherever the jailor is (the stolen goods are always in an evidence chest next to him). Just ask to visit a prisoner, and then he'll grumble and walk towards the door to let you into the jails.

While he's doing that, you can just sneak behind him, pick the very easy lock while he's opening the door and get your goods back. Then you can just walk out with a smug look on your face while the jailor's still opening the door for you. Problem solved.

Of course this doesn't work when there's two jailors there.

Another thing I've found handy is when the guard attempts to arrest you hit resist arrest, drop all of your stolen items, and then run far enough away so the guards can't pick up your things. I usually go to the next street to be safe. If you want them to stop attacking you, you have to hit yield first then let them arrest you.

Won't your bounty go up even more if you resist arrest though?

I've just found out that in all other cities, the evidence chests all have a very easy lock on it, but in Imperial Prison, it doesn't have a lock at all. Don't you find that odd?

Well, I'm not sure about this. (I'm always too lawful or avoid getting caught in the first place)

Anyway, today I just happened to be wandering about the market district when I overheard a rumour about the Imperial Watch being corrupt. I then got a message about a new topic which was about this corruption, which suggests I've stumbled upon a quest.

Now I haven't followed up on the quest but here is a possible explanation. If the watch is corrupt as the rumour goes (and rumours are pretty much always right in games.), then the nonlocked chest might be a symptom. Imagine the following exchange.

"Stop, criminal. It's off to jail with you. "
"Is that really necessary? If you would just let me walk, I could make it worth your while. "
"Deal. Now I'm going to take you to the prison so we can get the forms filled out. All stolen items will be confiscated. Now here is what is not going to happen. You will not hear from me that we will place your items in a chest that is easy to get to. I will also refuse to tell you that this chest is the one chest that does not have a lock. Now follow me, criminal."

So yeah, maybe there is no lock on the chest because the guards are basically turning a blind eye to all the criminals who want to recover their loot.

The other possible reason I can come up with is the more likely one but rather stupid. Bethesda forgot to put a lock on it.

Hehe jack I won't spoil that quest for you cos' it's a gooden (the surprise at the end is well...let's just say very suprising).

I could imagine the exchange between bethesda

"Hey you want to actually listen to the people's demands and make a mod that allows horseback fighting?"

"Yeh sure why not - uh oh, looks like we've forgot to lock the Imperial Prison Evidence Chest, lets just waste our time doing that instead. Can't have the thugs of Cyrodiil getting their swag back so easily..."

The difficulty on the lock depends on what level you are on.
Anyway, he wont notice that you steal your items back as he is sitting on his chair which is pointing away from the chest. Therefore, no need to ask him to visit a prisoner.

I'm a level 40 Nord and the locks are still very easy and in the case of Imperial Prisons, none at all.

And in many of the city prisons, the jailor is directly beside the chests, so you can still be seen.

It's simple to get your loot. Like, in Bruma, The door to the dungeon is right next to the chest. Still, it's a piece of cake:

Stand directly in front of the chest, but not in the way of the door. Tell the jailor that you wanna see a prisoner. as soon as you ask, go into sneak mode, face the chest, and when the eye thing goes dark, pick the lock. I've had to do this a lot 'cuz for some reason, all of my characters (and i have like 15) have an obsession w/ stealing and for some reason, I can't pickpocket ppl right, so I get put 'In Jail'.

ROFL !!!

Your characters, Shadow? Or do you mean you?

LOL LOL LOL. Seriously, Shadow, I know you, and it's not your characters that have trouble with stealing, it's you!!!!!! HAHAHAHAHAHAHAHA!!!!! You're very funny.

Chuckle chuckle.....